NZ540791A - Novel 2-pyridinecarboxamide derivatives - Google Patents

Novel 2-pyridinecarboxamide derivatives

Info

Publication number: NZ540791A
Authority: NZ; New Zealand
Prior art keywords: triazole; pyridine; phenylsulfanyl; group; methyl
Prior art date: 2003-02-13

Application number

NZ540791A

Other languages

English (en)

Inventor

Morihiro Mitsuya

Makoto Bamba

Fumiko Sakai

Hitomi Watanabe

Yasuhiro Sasaki

Teruyuki Nishimura

Jun-Ichi Eiki

Original Assignee

Banyu Pharma Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-02-13

Filing date

2004-02-13

Publication date

2009-09-25

2004-02-13 Application filed by Banyu Pharma Co Ltd filed Critical Banyu Pharma Co Ltd

2009-09-25 Publication of NZ540791A publication Critical patent/NZ540791A/en

Links

IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title claims description 19
150000001875 compounds Chemical class 0.000 claims abstract description 478
-1 pyridothiazolyl Chemical group 0.000 claims abstract description 259
150000003839 salts Chemical class 0.000 claims abstract description 52
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 24
125000001424 substituent group Chemical group 0.000 claims abstract description 21
125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
125000000335 thiazolyl group Chemical group 0.000 claims abstract description 10
125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 9
208000008589 Obesity Diseases 0.000 claims abstract description 7
235000020824 obesity Nutrition 0.000 claims abstract description 7
125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 7
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 5
125000001425 triazolyl group Chemical group 0.000 claims abstract description 5
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 4
238000002330 electrospray ionisation mass spectrometry Methods 0.000 claims description 163
238000006243 chemical reaction Methods 0.000 claims description 117
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
125000000217 alkyl group Chemical group 0.000 claims description 54
229920006395 saturated elastomer Polymers 0.000 claims description 44
108010021582 Glucokinase Proteins 0.000 claims description 39
238000003756 stirring Methods 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 26
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 25
238000000746 purification Methods 0.000 claims description 25
125000003396 thiol group Chemical group [H]S* 0.000 claims description 25
229940055764 triaz Drugs 0.000 claims description 25
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 23
150000003857 carboxamides Chemical class 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
239000012044 organic layer Substances 0.000 claims description 22
238000010898 silica gel chromatography Methods 0.000 claims description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
239000003814 drug Substances 0.000 claims description 17
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
229910000027 potassium carbonate Inorganic materials 0.000 claims description 13
230000000694 effects Effects 0.000 claims description 12
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 10
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 10
238000010992 reflux Methods 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 9
239000012043 crude product Substances 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
KFGYICCMRNBNOA-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)sulfanyl-n-(3-methyl-1,2,4-thiadiazol-5-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound CC1=NSC(NC(=O)C=2C(=CC=C(SC=3NC=NN=3)N=2)SC=2C=NC(C)=CC=2)=N1 KFGYICCMRNBNOA-UHFFFAOYSA-N 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
DSTFHGBZUCEGQU-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfanyl-6-[(5-methyl-1h-1,2,4-triazol-3-yl)sulfanyl]-n-(1,3-thiazol-2-yl)pyridine-2-carboxamide Chemical compound N1C(C)=NN=C1SC(N=C1C(=O)NC=2SC=CN=2)=CC=C1SC1=CC=C(F)C=C1 DSTFHGBZUCEGQU-UHFFFAOYSA-N 0.000 claims description 5
AXASQQUGTGUMPJ-UHFFFAOYSA-N 3-[4-[2-(dimethylamino)ethoxy]phenyl]sulfanyl-6-[(5-methyl-1h-1,2,4-triazol-3-yl)sulfanyl]-n-(1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide Chemical compound C1=CC(OCCN(C)C)=CC=C1SC(C(=N1)C(=O)NC=2SN=CN=2)=CC=C1SC1=NN=C(C)N1 AXASQQUGTGUMPJ-UHFFFAOYSA-N 0.000 claims description 5
102000004877 Insulin Human genes 0.000 claims description 5
108090001061 Insulin Proteins 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
229940125396 insulin Drugs 0.000 claims description 5
NXGDLXQQZWZIPG-UHFFFAOYSA-N n-[4-(methoxymethyl)-1,3-thiazol-2-yl]-3-(4-methoxyphenyl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound COCC1=CSC(NC(=O)C=2C(=CC=C(SC=3NC=NN=3)N=2)SC=2C=CC(OC)=CC=2)=N1 NXGDLXQQZWZIPG-UHFFFAOYSA-N 0.000 claims description 5
PNDILIXGHBOIKV-UHFFFAOYSA-N 3-(6-ethoxypyridin-3-yl)sulfanyl-n-(3-methyl-1,2,4-thiadiazol-5-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=NC(OCC)=CC=C1SC(C(=N1)C(=O)NC=2SN=C(C)N=2)=CC=C1SC1=NN=CN1 PNDILIXGHBOIKV-UHFFFAOYSA-N 0.000 claims description 4
208000002249 Diabetes Complications Diseases 0.000 claims description 4
229940126033 PPAR agonist Drugs 0.000 claims description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 4
239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
KKSVKMVNJDXTOL-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfanyl-n-(4-methyl-1,3-thiazol-2-yl)-6-phenoxypyridine-2-carboxamide Chemical compound CC1=CSC(NC(=O)C=2C(=CC=C(OC=3C=CC=CC=3)N=2)SC=2C=CC(F)=CC=2)=N1 KKSVKMVNJDXTOL-UHFFFAOYSA-N 0.000 claims description 3
KRWCYUXKLUSDFK-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)sulfanyl-6-(1h-pyrazol-4-ylsulfanyl)-n-(1,3-thiazol-2-yl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC=C1SC(C(=N1)C(=O)NC=2SC=CN=2)=CC=C1SC1=CNN=C1 KRWCYUXKLUSDFK-UHFFFAOYSA-N 0.000 claims description 3
JADPOZIPXGRFTI-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)sulfanyl-n-(1,2,4-thiadiazol-5-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC=C1SC(C(=N1)C(=O)NC=2SN=CN=2)=CC=C1SC1=NN=CN1 JADPOZIPXGRFTI-UHFFFAOYSA-N 0.000 claims description 3
LIEVWHSVQUXFRT-UHFFFAOYSA-N 3-[4-(dimethylcarbamoyl)phenyl]sulfanyl-n-(1,2-oxazol-3-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1SC(C(=N1)C(=O)NC2=NOC=C2)=CC=C1SC1=NN=CN1 LIEVWHSVQUXFRT-UHFFFAOYSA-N 0.000 claims description 3
IJDKTUMJQUTOOS-UHFFFAOYSA-N 3-[4-(methoxymethyl)phenyl]sulfanyl-n-(1,3-thiazol-2-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(COC)=CC=C1SC(C(=N1)C(=O)NC=2SC=CN=2)=CC=C1SC1=NN=CN1 IJDKTUMJQUTOOS-UHFFFAOYSA-N 0.000 claims description 3
102000005157 Somatostatin Human genes 0.000 claims description 3
108010056088 Somatostatin Proteins 0.000 claims description 3
241000534944 Thia Species 0.000 claims description 3
239000000706 filtrate Substances 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 claims description 3
229960000553 somatostatin Drugs 0.000 claims description 3
LQQZDRRSGJBHRW-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)-n-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1SC(C(=N1)C(=O)NC=2SC=C(N=2)C(F)(F)F)=CC=C1SC1=NN=CN1 LQQZDRRSGJBHRW-UHFFFAOYSA-N 0.000 claims description 2
LHZNQSCUQGCZIX-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)sulfanyl-6-[(5-oxo-1,2-dihydro-1,2,4-triazol-3-yl)sulfanyl]-n-(1,3-thiazol-2-yl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC=C1SC(C(=N1)C(=O)NC=2SC=CN=2)=CC=C1SC1=NN=C(O)N1 LHZNQSCUQGCZIX-UHFFFAOYSA-N 0.000 claims description 2
DRSBBXJNBSGSLE-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)sulfanyl-n-(1,3-thiazol-2-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC=C1SC(C(=N1)C(=O)NC=2SC=CN=2)=CC=C1SC1=NN=CN1 DRSBBXJNBSGSLE-UHFFFAOYSA-N 0.000 claims description 2
JKAPUBSEIXHXFX-UHFFFAOYSA-N 3-[4-(dimethylcarbamoyl)phenyl]sulfanyl-n-(1,3-thiazol-2-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1SC(C(=N1)C(=O)NC=2SC=CN=2)=CC=C1SC1=NN=CN1 JKAPUBSEIXHXFX-UHFFFAOYSA-N 0.000 claims description 2
WFNDASFYWZBVDN-UHFFFAOYSA-N 3-[4-(methoxymethyl)phenyl]sulfanyl-n-(1-methylpyrazol-3-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(COC)=CC=C1SC(C(=N1)C(=O)NC2=NN(C)C=C2)=CC=C1SC1=NN=CN1 WFNDASFYWZBVDN-UHFFFAOYSA-N 0.000 claims description 2
QLRZGBAAHNZERG-UHFFFAOYSA-N 3-[4-(methylcarbamoyl)phenyl]sulfanyl-n-(1,3-thiazol-2-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1SC(C(=N1)C(=O)NC=2SC=CN=2)=CC=C1SC1=NN=CN1 QLRZGBAAHNZERG-UHFFFAOYSA-N 0.000 claims description 2
FDZJJKMCFQYNGJ-UHFFFAOYSA-N 3-[4-[2-(dimethylamino)ethoxy]phenyl]sulfanyl-n-(3-methyl-3h-1,2,4-thiadiazol-2-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound CC1N=CSN1NC(=O)C1=NC(SC=2NC=NN=2)=CC=C1SC1=CC=C(OCCN(C)C)C=C1 FDZJJKMCFQYNGJ-UHFFFAOYSA-N 0.000 claims description 2
229940122199 Insulin secretagogue Drugs 0.000 claims description 2
229940124828 glucokinase activator Drugs 0.000 claims description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
NECIKMLFFIOHGL-UHFFFAOYSA-N n-(4-acetyl-1,3-thiazol-2-yl)-3-(4-methoxyphenyl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1SC(C(=N1)C(=O)NC=2SC=C(N=2)C(C)=O)=CC=C1SC1=NN=CN1 NECIKMLFFIOHGL-UHFFFAOYSA-N 0.000 claims description 2
LRYFMFUERAVXHD-UHFFFAOYSA-N n-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-3-(4-methoxyphenyl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1SC(C(=N1)C(=O)NC=2SC(CO)=CN=2)=CC=C1SC1=NN=CN1 LRYFMFUERAVXHD-UHFFFAOYSA-N 0.000 claims description 2
150000002496 iodine Chemical class 0.000 claims 2
NNISESGLGYXCDT-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)-n-[5-(trifluoromethyl)-1,3-thiazol-2-yl]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1SC(C(=N1)C(=O)NC=2SC(=CN=2)C(F)(F)F)=CC=C1SC1=NN=CN1 NNISESGLGYXCDT-UHFFFAOYSA-N 0.000 claims 1
OGRDRPHSMRDSRO-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfanyl-n-(1,2-oxazol-3-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1SC(C(=N1)C(=O)NC2=NOC=C2)=CC=C1SC1=NN=CN1 OGRDRPHSMRDSRO-UHFFFAOYSA-N 0.000 claims 1
KDTPIRGNRJLZGT-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfanyl-n-(1,3-thiazol-2-yl)-6-(1h-1,2,4-triazol-5-yl)pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C=2NC=NN=2)N=C1C(=O)NC1=NC=CS1 KDTPIRGNRJLZGT-UHFFFAOYSA-N 0.000 claims 1
IMKDRWYDCAZVDM-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)sulfanyl-n-(4-methyl-1,3-thiazol-2-yl)-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound CC1=CSC(NC(=O)C=2C(=CC=C(SC=3NC=NN=3)N=2)SC=2C=NC(C)=CC=2)=N1 IMKDRWYDCAZVDM-UHFFFAOYSA-N 0.000 claims 1
UYXGQGDQDFFSGE-UHFFFAOYSA-N 5-methoxy-2-methylbenzenethiol Chemical compound COC1=CC=C(C)C(S)=C1 UYXGQGDQDFFSGE-UHFFFAOYSA-N 0.000 claims 1
PGLIUCLTXOYQMV-UHFFFAOYSA-N Cetirizine hydrochloride Chemical compound Cl.Cl.C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 PGLIUCLTXOYQMV-UHFFFAOYSA-N 0.000 claims 1
102000030595 Glucokinase Human genes 0.000 claims 1
GXWNSBRRUGKIRS-UHFFFAOYSA-N ethyl 2-[[3-(4-methoxyphenyl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carbonyl]amino]-1,3-thiazole-5-carboxylate Chemical compound S1C(C(=O)OCC)=CN=C1NC(=O)C1=NC(SC=2NC=NN=2)=CC=C1SC1=CC=C(OC)C=C1 GXWNSBRRUGKIRS-UHFFFAOYSA-N 0.000 claims 1
SAYJADHJJPWZFH-UHFFFAOYSA-N n-(3-cyclopropyl-1,2,4-thiadiazol-5-yl)-3-(6-methylpyridin-3-yl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC=C1SC(C(=N1)C(=O)NC=2SN=C(N=2)C2CC2)=CC=C1SC1=NN=CN1 SAYJADHJJPWZFH-UHFFFAOYSA-N 0.000 claims 1
FZGRFOWZEYCBAL-UHFFFAOYSA-N n-(3-methoxy-1,2,4-thiadiazol-5-yl)-3-(6-methylpyridin-3-yl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound COC1=NSC(NC(=O)C=2C(=CC=C(SC=3NC=NN=3)N=2)SC=2C=NC(C)=CC=2)=N1 FZGRFOWZEYCBAL-UHFFFAOYSA-N 0.000 claims 1
YSAAKVDDZZGABH-UHFFFAOYSA-N n-(4,5-dimethyl-1,3-thiazol-2-yl)-3-(4-methoxyphenyl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1SC(C(=N1)C(=O)NC=2SC(C)=C(C)N=2)=CC=C1SC1=NN=CN1 YSAAKVDDZZGABH-UHFFFAOYSA-N 0.000 claims 1
GRUDLLKKXBRWKY-UHFFFAOYSA-N n-[3-(hydroxymethyl)-1,2,4-thiadiazol-5-yl]-3-(6-methylpyridin-3-yl)sulfanyl-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC=C1SC(C(=N1)C(=O)NC=2SN=C(CO)N=2)=CC=C1SC1=NN=CN1 GRUDLLKKXBRWKY-UHFFFAOYSA-N 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 abstract description 11
238000004519 manufacturing process Methods 0.000 description 659
238000000034 method Methods 0.000 description 536
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 150
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 139
101150041968 CDC13 gene Proteins 0.000 description 133
HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 126
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
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RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 51
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 42
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125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229960002277 tolazamide Drugs 0.000 description 1
OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
229960001729 voglibose Drugs 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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NZ540791A 2003-02-13 2004-02-13 Novel 2-pyridinecarboxamide derivatives NZ540791A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP2003034987		2003-02-13
JP2003342860		2003-10-01
JP2004014799		2004-01-22
PCT/JP2004/001568 WO2004081001A1 (ja)	2003-02-13	2004-02-13	新規２－ピリジンカルボキサミド誘導体

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NZ540791A true NZ540791A (en)	2009-09-25

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NZ540791A NZ540791A (en)	2003-02-13	2004-02-13	Novel 2-pyridinecarboxamide derivatives

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US (3)	US7629362B2 (es)
EP (1)	EP1598349B1 (es)
JP (1)	JP4400563B2 (es)
KR (1)	KR20050101208A (es)
AR (1)	AR045414A1 (es)
AT (1)	ATE517887T1 (es)
AU (2)	AU2004220234C1 (es)
BR (1)	BRPI0407283A (es)
CA (1)	CA2515841C (es)
EC (1)	ECSP056016A (es)
IL (1)	IL169905A0 (es)
MA (1)	MA27626A1 (es)
MX (1)	MXPA05008619A (es)
NO (1)	NO20054224L (es)
NZ (1)	NZ540791A (es)
PE (1)	PE20050194A1 (es)
TW (1)	TWI336329B (es)
UA (1)	UA82867C2 (es)
WO (1)	WO2004081001A1 (es)
ZA (1)	ZA200504852B (es)

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2004
- 2004-02-13 NZ NZ540791A patent/NZ540791A/en not_active IP Right Cessation
- 2004-02-13 TW TW093103493A patent/TWI336329B/zh not_active IP Right Cessation
- 2004-02-13 AT AT04711025T patent/ATE517887T1/de not_active IP Right Cessation
- 2004-02-13 KR KR1020057014827A patent/KR20050101208A/ko not_active Ceased
- 2004-02-13 WO PCT/JP2004/001568 patent/WO2004081001A1/ja not_active Ceased
- 2004-02-13 UA UAA200508682A patent/UA82867C2/uk unknown
- 2004-02-13 AR ARP040100442A patent/AR045414A1/es unknown
- 2004-02-13 AU AU2004220234A patent/AU2004220234C1/en not_active Ceased
- 2004-02-13 CA CA2515841A patent/CA2515841C/en not_active Expired - Fee Related
- 2004-02-13 BR BR0407283-9A patent/BRPI0407283A/pt not_active Application Discontinuation
- 2004-02-13 EP EP04711025A patent/EP1598349B1/en not_active Expired - Lifetime
- 2004-02-13 JP JP2005503465A patent/JP4400563B2/ja not_active Expired - Fee Related
- 2004-02-13 MX MXPA05008619A patent/MXPA05008619A/es active IP Right Grant
- 2004-02-13 PE PE2004000159A patent/PE20050194A1/es not_active Application Discontinuation
- 2004-02-13 US US10/545,424 patent/US7629362B2/en active Active
2005
- 2005-06-14 ZA ZA2005/04852A patent/ZA200504852B/en unknown
- 2005-07-26 IL IL169905A patent/IL169905A0/en unknown
- 2005-08-24 MA MA28455A patent/MA27626A1/fr unknown
- 2005-09-12 NO NO20054224A patent/NO20054224L/no not_active Application Discontinuation
- 2005-09-13 EC EC2005006016A patent/ECSP056016A/es unknown
2009
- 2009-10-23 US US12/604,835 patent/US8344003B2/en not_active Expired - Lifetime
2010
- 2010-01-04 AU AU2010200004A patent/AU2010200004B2/en not_active Ceased
2012
- 2012-11-27 US US13/685,775 patent/US8765789B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU2004220234B2 (en)	2009-11-26
US20130085156A1 (en)	2013-04-04
ECSP056016A (es)	2006-01-27
MXPA05008619A (es)	2005-11-04
JPWO2004081001A1 (ja)	2006-06-08
ATE517887T1 (de)	2011-08-15
JP4400563B2 (ja)	2010-01-20
US8765789B2 (en)	2014-07-01
EP1598349A1 (en)	2005-11-23
TW200510381A (en)	2005-03-16
CA2515841C (en)	2010-06-01
AU2004220234C1 (en)	2013-01-17
CA2515841A1 (en)	2004-09-23
HK1088602A1 (zh)	2006-11-10
NO20054224D0 (no)	2005-09-12
US7629362B2 (en)	2009-12-08
NO20054224L (no)	2005-11-10
KR20050101208A (ko)	2005-10-20
BRPI0407283A (pt)	2006-01-31
EP1598349A4 (en)	2008-12-31
AU2004220234A1 (en)	2004-09-23
AR045414A1 (es)	2005-10-26
UA82867C2 (en)	2008-05-26
AU2010200004A1 (en)	2010-01-28
TWI336329B (en)	2011-01-21
EP1598349B1 (en)	2011-07-27
US20100041660A1 (en)	2010-02-18
MA27626A1 (fr)	2005-11-01
WO2004081001A1 (ja)	2004-09-23
PE20050194A1 (es)	2005-04-23
US8344003B2 (en)	2013-01-01
ZA200504852B (en)	2006-05-31
IL169905A0 (en)	2007-07-04
US20060258701A1 (en)	2006-11-16
AU2010200004B2 (en)	2012-07-19

Legal Events

Date	Code	Title	Description
2008-01-31	RENW	Renewal (renewal fees accepted)
2010-01-29	PSEA	Patent sealed
2011-01-28	RENW	Renewal (renewal fees accepted)
2013-12-20	RENW	Renewal (renewal fees accepted)	Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 13 FEB 2017 BY THOMSON REUTERS Effective date: 20131218
2017-08-25	LAPS	Patent lapsed

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